74 habits conversation starters and questions to spark meaningful conversations

I love talking about habits. It’s one of the easiest topics to start a conversation and keep it going. Why? 

a) We are all creatures of habit.

MIT revealed that “a good 90 percent of what most people do in any day follows routines so complete that their behavior can be predicted with just a few mathematical equations.” 

b) There’s been a flood of habit books in the market.

People generally understand that habits have the power to transform our lives. 

In this article, I will share a list of habits conversation starters and questions that you can use in different social situations.

What makes me uniquely qualified to write about this? 

Over the last ten years — across three continents — I’ve started conversations with thousands of strangers. I’ve also interviewed well over 700 people for my projects (namely a street journalism project and a book). 

Speaking about my experience talking with strangers at TEDx! 

In other words, I’ve asked more questions to spark meaningful conversations than most people. 

And, habit-setting happens to be a topic that I’m intimately familiar with: 

• I’ve worked with my former business partner to help thousands of entrepreneurs and professionals improve their learning habits.

• I’ve stayed consistent with my healthy habits like exercise and meditation since 2019.

• I’ve also broken tough habits like addiction (thanks to my therapist, Sean Swaby!)

When and how to use these questions 

No hard rules per se, but here are a few suggestions:

• Ask questions about someone’s habits after you’ve built some rapport with them. After all, your habits reveal how you spend your time and what you see as important.

• Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.

• Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation 🙂 I’ve been guilty of that.

• Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.
  
  Why is that important? Different people have different ways of saying things. The more you can tailor the conversation starter to your tone of voice, personality etc., the easier (read: less awkward) you will find using it.

  To make this more usable for you, I’ve tried introducing variations of the same question 🙂

With that said, let’s jump in! 

Conversation starters about career habits

Small talk 

1. What’s the first thing you do when you get into the office? 
2. What do you usually do during your lunch break? 
3. What do you always do to prepare for your meetings?
4. What’s the last thing you do before leaving the office? 
5. What’s the first thing you do to relax after work?
6. What’s your go-to habit to combat Monday blues?
7. What’s your #1 habit to handle a stressful day/week?

Deeper questions 

1. How do your habits impact your career? 
2. What percentage of your career success would you attribute to habits?
3. What are your top five work habits and why? 
4. What’s the most important habit across all your different jobs? 
5. What’s the #1 habit that great employees/leaders have?
6. What’s the most effective communication habit that you’ve learned? 
7. What habit has helped you become more productive at work?
8. What’s one habit that has transformed your career?
9. What work habit would you like to adopt/become more consistent at?
10. To achieve <specific career goal>, what habit do you need to get rid of?

Conversation starters about goal-related habits

Small talk 

1. What’s the first thing you do when you wake up? 
2. What’s the last thing you do before you sleep? 
3. What’s one thing you do every morning/afternoon/night?
4. What’s one thing you always do over the weekend? 

Deeper questions 

1. How do your habits impact your success? 
2. What percentage of your success would you attribute to habits?
3. What are your top five habits and why? 
4. What’s the most important habit across all your goals? 
5. What habit has helped you become more productive/happier/more successful?
6. What’s the one habit that has transformed your life? 
7. What habit do you need to adopt to achieve <specific goal>?
8. To achieve <specific goal>, what habit do you need to get rid of?
9. What habit do you feel most proud of?
10. What habit do you feel a bit guilty about?
11. Knowing what you know about yourself, how would you make sure that you follow through with a new habit?  

Related article: 54 goals conversation starters to spark deep conversations

Conversation starters about studying habits 

Small talk 

1. What do you always do before a new semester/academic year?
2. Do you prefer handwriting your notes or typing them out? 
3. How do you usually take notes in classes? 
4. What do you usually do to prepare for an exam?
5. What do you enjoy doing to relax after class? 

Deeper questions 

1. What’s the one habit that has helped you ace your classes?
2. What habit has helped you memorize better?  
3. What’s the most underrated study habit in your opinion?
4. What non-study habit has helped your studies the most?
5. What’s the biggest difference between how you study now vs. how you studied in high school?

For more ways to start conversations with students:7 easy ways to talk to strangers on campus (without being awkward)

Conversation starters about exercise habits

Small talk 

1. How often do you work out/run etc.? 
2. Where else do you work out/run etc.?
3. Is there a personal trainer you would recommend?
4. Do you prefer working out alone or with others? 
5. Do you listen to music while working out? Why / why not?

Deeper questions 

1. What helps you stay consistent with your workout routine? // How do you stay motivated in your workout? 
2. What’s your biggest challenge in staying consistent?
3. Why do you think most people don’t consistently exercise? 

Conversation starters about coffee habits 

Small talk

1. What’s your go-to morning drink? 
2. Are you a coffee or tea person? Or neither? 
3. Do you need a morning cuppa to start your day? 
4. How often do you drink coffee every day? 
5. Decaf – yay or nay? 

Deeper questions 

1. Have you ever tried going a full day without coffee? 
2. Why do so many people need coffee to function?
3. What do you think would happen if the world ran out of coffee? 

Conversation starters about drinking habits 

Small talk 

1. What’s your go-to drink? 
2. Are you a wine, beer, or spirits person? 
3. How often do you drink? 
4. Do you ever get hangovers? 
5. What’s the best food after drinks? // What’s your favorite hangover food? 

Deeper questions 

1. What are you like when drunk? 
2. Do you ever drink alone? Why or why not? 
3. What would you say is the national alcohol of your country?

Conversation starters about traveling habits

Small talk 

1. Do you prefer flying or taking the train?
2. What do you always do in a new city/country? // What do you never do in a new city/country?
3. Have you ever tried backpacking? // Would you ever try backpacking? 
4. Do you work out while traveling? // Do you talk to locals while traveling? 

Deeper questions 

1. Would you rather travel to as many places as possible, or travel to only one place?  
2. Would you rather travel to a new country or your favorite country?
3. Would you rather travel alone or with others?
4. What’s your favorite habit while you travel?
5. What’s one traveling habit that you hate? 
6. What’s the most underrated traveling habit in your opinion? 

For more ways to start conversations on a plane, check out 7 easy ways to talk to strangers on a plane